This article originally appeared in the March 2011 issue of Architectural Digest.

Sheryl Crow’s family compound in the Hollywood Hills is the stuff of California dreams: mountain trails, ocean views, massive date palms, hillsides covered in cacti, red-tailed hawks flying in lazy circles above, a sun-baked metropolis sprawling in the distance below. It’s also something of an architectural history lesson, with each of the three homes on the meandering 11-acre property modeling a distinct style of early Los Angeles residential design. There’s the 1926 Spanish Colonial hacienda that Crow shares with her two sons, three-year-old Wyatt and baby Levi; a 1909 Craftsman bungalow; and a picturesque 19th-century cottage—the latter two used as guesthouses for friends, relatives, and members of the Grammy-winning singer-songwriter’s band. “This is an incredibly magical place,” Crow says. “It has the best of everything California has to offer, but there’s also something deeper. The land has a fascinating energy.”

Crow purchased the Spanish Colonial in 1997, fresh off the success of her self-titled follow-up to her hugely popular debut album, Tuesday Night Music Club. Two years later, with her fortunes in the music business continuing to rise, she acquired the adjoining property with the cottage and bungalow. “I was drawn to it instantly,” she says of the main house. “The foyer in particular is grand but warm and slightly exotic. I grew up in Missouri, where you don’t really see architecture like this.”

Faced with the daunting prospect of furnishing the home while tending to the demands of her burgeoning career, Crow engaged the services of a professional designer, but the collaboration was short-lived. The designer sent over an antique rug that cost more than the project’s entire budget, and the musician knew the relationship wasn’t going to work.

Singer-songwriter Sheryl Crow at home in the Hollywood Hills; the infinity-edge pool, designed by Jonny Appleseed Landscaping, overlooks Los Angeles.

Living in the home for roughly a year with almost no furniture gave Crow a feel for its airy spaces, poetic light, and uniquely Californian character. Slowly, guided more by intuition than formal adherence to any specific period or style of decorating, she began to fill the rooms herself, piece by piece, taking a highly personal, richly layered approach to interior design.

Crow gathered much of what she was after when touring. “On the road I’m always on the lookout for great things,” she says. “I have a big following in France, and on one of my trips to Paris I found a set of eight club chairs at a flea market. They were classic Deco—and a real bargain,” she adds with a hint of triumph.

Against a backdrop of white stucco walls and floors that alternate between ebony-stained wood and terra-cotta tiles, Crow’s furnishings are an ensemble performance—unpretentious American and Continental furniture, vintage industrial lights, antique dress forms, skulls, and artist’s mannequins. “I’m a collector of oddities,” she says, “stuff that is somehow off-center or off-kilter, things that have their own inner lives and implore you to use your imagination.” Latin American santos and other forms of religious art hark back to her upbringing. “I grew up going to church,” she says, “so the religious works really speak to me.”

Pride of place above the mantel in the living room belongs to a 19th-century iron-and-wood “boneshaker” bicycle, so named for its decidedly non-ergonomic design. She found it, and many other of her prized pieces, at the Venice, California, boutique Obsolete, a wonderland of Victoriana, spooky artifacts, and contemporary items with a steampunk aesthetic. Ray Azoulay, the shop’s exuberant owner, describes Crow as an ideal client. “She has an extremely discerning eye and an obvious affinity for the things I’m drawn to,” he says. “There’s a fearlessness and a bit of irreverence in her style, but that’s what makes it so refreshing.”

So many conversation pieces speaking at once could run the risk of decorative overkill, but the effect of Crow’s design is quite the opposite. The compositions are restrained and harmonious. “They’re like an art installation,” she says of the three houses, “always evolving and adapting to the passage of time and the changes in my life.” The sense of serenity here is heightened by the lush landscaping visible through the windows and doors, as well as the tepee and swing set on the lawn and other signs of contented family life. The unfolding view also contributes to the fascinating energy Crow talks about—or, to borrow a phrase from her latest album, 100 Miles from Memphis, that free, peaceful feeling.

“There are a lot of people who think of me as very straight, very middle America and conventional,” Crow says, “so I imagine this place will come as a surprise. I’d hope it would make them think, I need to get to know this person better.”

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